• Thermolysis of some N-arylbenzamidoximes: Mechanistic studies for formation of anilide, oxazole and imidazole derivatives

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    • Keywords


      Thermolysis; rearrangement; N-2-pyridyl- and N-Α-Naphthylbenz- amidoxime; imidazo- and oxazolo derivatives.

    • Abstract


      The thermolysis of N-2-pyridylbenzamidoxime I under nitrogen atmosphere for 5 hours givesrise to 2-phenyl-1H-imidazo[4,5-b]pyridine and N-(pyridin-2-yl)benzamide as the major products (52.4and 18.11%, respectively), in addition to 2-hydroxy pyridine, benzonitrile, benzoic acid, 2-aminopyridine,2-phenyloxazolo[4,5-b]pyridine, 9H-pyrrolo[2,3-b:5,4-b']dipyridine and 2,4,6-triphenyl-1,3,5-triazine. Also,heating N-Α-naphthylbenzamidoxime II under the same conditions gave N-(Α-Naphthyl)benzamide, 2-Phenyl-3H-naphtho[2,1-d] imidazole as the major products besides benzonitrile, benzoic acid, Α-naphthylamine and2-phenylnaphtho[1,2-d]oxazole. In the presence of tetralin, I gave 1-hydroxytetralin, Α-tetralone and 1,1'-bitetrayl besides the previous products. The reaction and isolated products have been interpreted in terms of afree radical mechanism involving the homolysis of N-O and/or C-N bonds.

    • Author Affiliations



      1. Chemistry Department, Faculty of Science, Assiut University, Assiut 71516, Egypt
      2. Chemistry Department, Faculty of Science, King Abdulaziz University, Jeddah 21589, Saudi Arabia
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